


Leaving the comfort-zone

by marlowe78



Category: Supernatural
Genre: Anal Sex, Awkward Sexual Situations, First Time, M/M, Schmoop, Wincest - Freeform, non-sexy sex
Language: English
Status: Completed
Published: 2015-07-25
Updated: 2015-07-25
Packaged: 2018-04-11 04:19:02
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,517
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4421066
Author URL: https://archiveofourown.org/users/marlowe78/pseuds/marlowe78
Summary: <blockquote class="userstuff">
              <p>Trying for something a bit more, the Winchesters realize that for them, more isn't really all that awesome.</p>
            </blockquote>





	Leaving the comfort-zone

**Author's Note:**

> Disclaimer: Not mine. Just borrowing. Will return undamaged and won't demand pay.
> 
> Damn! I forgot! This whole thing wouldn't be here if my friend soncnica hadn't encouraged me and looked over it to find flaws. So thank you, babe, for being my beta!
> 
> a/n:  
> Right. Ok. This is my very first and very likely ONLY porn-based fic, and I'm 99% sure the only wincest I'll ever write.
> 
> It's just not my personal comfort-zone, and I think it's not what we see on the show. So, whatever.
> 
> I still wrote this, because I do like reading porny ficlets that involve Dean and Sam (who says I'm rational?). I mostly wrote this, because I really wanted to read a ficlet like that. It wasn't there, so I wrote it myself. If you find another one with similar content, please send me the link, I'd be very interested.
> 
> Ok, 'nough talk. On with the sex...

****************  
There was a problem in their relationship. Well, not so much a problem as a hitch, a slight bump on the road that was supposed to lead to freaking great sex and, by that way, to a healthy, normal relationship.

Can you say ‘normal’ when you’re referring to a relationship that features fucking and being in love with your brother? Would it be in any way more normal if Sammy were a girl, like, a real girl, with boobs?

Probably not, Dean thought. You know, whenever he did think about that kind of stuff, which was rare since it was usually followed by a severe freak-out.

After all, this wasn’t only his best friend, partner, a good-looking guy with damn sexy body-parts! This was his freaking _brother_! The kid he went to school with, whom he fought with, tackled with. Whom he’d allowed to wipe his snotty nose in his favorite shirt more often than not – and he totally wouldn’t ever let him do that again! – and whom he loved in more ways than anyone could ever, ever believe and understand.

It was also the child he’d watched grow up – hell, he’d practically raised that brat. He was the lanky teenager with too-big feet, there to tease and to protect and to drive crazy. The kid he’d watched being devastated by his girl’s death, overwhelmed with grief and sorrow and fear for his own life, for his future.

And, most importantly, it was the man who had driven himself crazy to get Dean out of that fucking crossroads-deal, who’d tried to sell his own soul and who had, in a way, done just that when he’d let Ruby poison his mind in order to bring something like _justice_ to the world.

Yeah, he was still pissed about that. And not in some twisted case of jealousy, because Dean hadn’t been thinking of Sam that way then.

That man in the bathroom was also a hero, the man who saved the world by sacrificing his life and soul to get Lucifer back into the cage. And yes, Dean still felt incredible guilty about that, because no matter how you looked at it, if he hadn’t been such a needy asshole, he wouldn’t have sold his soul, Sam wouldn’t have been desperate and alone and that whole fucking crap wouldn’t have happened.

So, still wondering why Dean usually thought as rarely as possible about the relationship he was in?  
He rather just didn’t, and in bed, Sam wasn’t Sammy anymore. He became "Sam", or "bitch" or "chick" when he was being a whiny princess again, but _Sammy_ was the boy Dean' had raised, and while he’d be kinda ok with consensual brotherly incest, parental incest was just so fucking wrong, there wasn’t a word to express how much. Everything like "perverted" didn't even come close.

Between the sheets, Sammy was Sam now, and he wasn’t his brother. He was his lover, his best friend and his companion, his soul-mate, if you wanted to get schmoopy, but he was _not_ the little brother anymore.

Fucked up?

Yeah, but what wasn’t in this world…

Any way you looked at it, he’d somewhere along the way fallen for Sam, and he’d fallen hard. No pun intended. Sam was freaking hot and smart and he knew him, knew him like nobody else ever had; and what was more important, he still loved him, no matter what.

And for some strange reason, he also thought Dean was someone desirable, even though he really knew all his secrets. Or, well, at least the really bad ones. About the panties? Nuh-uh. And he never would.

So, where was that glitch that was mentioned at the beginning?

Ah. Yeah. That glitch was mostly that there was no ‘glitching’. Because to top all that crap with being related and all, they also were very much straight.

Yeah, ok, obviously not all straight. But both of them loved pussy, loved the feel of it, and yepp, both had more than enough freaking steroids – no, not that, what’s the word… testosterone, yes. That one. - to consider themselves very manly men.

Uhm… yeah. Not that that was bad, or anything. And no, strangely enough, neither of them felt the urge to go and pick up girls because of that. Once they had done all that schmoopy crap about talking about feelings and all, they didn’t do that anymore.

Well, except for Lacey. Damn…. She’d been hot. But that was different, because they'd both had her, and though she’d had her fun as well, the kissing had stayed between Sam and him. Maybe they could do that again, some time?

But, the problem was, maybe because of that whole hormone-juice inside or because of their upbringing or just because, they were both very strictly tops.

************

_  
Dean was moaning, writhing like a cat in heat, or whatever cool animal did that kind of thing. He couldn’t form any thought anymore apart from ‘yes yes, please, yes yesyesyesyesyes!’ and he might have been a bit more vocal than usual._

_But they were alone in the forest, somewhere in a hunter’s cabin in Wisconsin. All alone, nobody there who might listen – not even that berserker anymore, not since yesterday – and a huge, comfortable mattress in the room._

_Sam was making him see stars, his long tongue driving him crazy, swirling around his nipples, and licking down his side, his abdomen and yes, disgustingly enough, into his bellybutton. And it felt like exploding! Sam’s teeth grazed his left nipple, the right hand teasing the other one and his left hand… his left hand was between his legs, fondling his dick and his balls, which made Dean whine like a bitch in heat and buck up into that huge, warm, slightly moist palm. He was falling apart. When Sam tweaked here, twisted there and squeezed just right, he came, like a tidal wave swooshing over him and making him scream and buck and crash and burn._

_When he came to, he felt Sam suck at his dick._

_A very, very pleasant sensation, because damn, Sam had a mouth on him… So he rested his eyes some more, certainly not above letting Sam have some fun down there, if he felt that way. Dean was pretty sure his dick wasn’t up for much right now, he wasn’t sixteen anymore, and it hadn’t been his first orgasm today. But that didn’t mean it might not become interested again._

_He scrunched up his face, though, as he recalled that Sam himself hadn’t come yet, and he kinda remembered how pissed he would get when Dean was being a selfish jerk again._

_So, reluctantly, he shifted, trying to gather some strength to get his hands down there, when he felt something unexpected. Kinda slippery, and not where anything had a business being._

_“Uh…Sam?”_

_“Hmmm” he answered around his dick and Dean moaned like a porn-star because the vibration made him nearly pass out._

_“Sam… what are you…” he spared himself the rest of the question, because that was the exact moment that there was a fucking finger in his ass! “Holy Fuck, get off” he growled, scrambling away._

_“That was kinda the idea” Sam had the balls to smirk – SMIRK – at him, his voice rough from blowing Dean the second time that day._

_“Oh yeah, if that’d been the goal, I’da sucked you off in the shower! But nooooo, Queen Sam didn’t want that” He pitched his voice high: “’Oh no, Dean, today is your special day, I’ll make you so happy today, just you…’. Lying, deceiving little bitch!”_

_“Deeeeaaan…”_

_“No!”_

_“Com’on. Dean, it’s supposed to be really good! I mean, people wouldn’t do it if it wasn’t. C’mon, man…” and damn him, Sam had the nerve to set his puppy-eyes at him, the traitor._

_“No.”_

_“Deeeaan, please”_

_“If it’s so damn good, why don’t YOU try it, huh?” He would not, not under any circumstance, tell Sam that he just didn’t think his brother’s hot but long and damn-big cock would fit. And nope, he wouldn’t admit that his own, while damn fine and much more hot and perfect dick would fit much better, if there had to be fitting involved. Not that there was that much difference, size-wise, but well, Sam was, after all, a few inches higher than him. Things tended to be proportional among the Winchesters._

_“I will, but right now, you’re the one all loose and happy,” he grabbed Dean’s cock and flapped it around some, grinning when Dean squeaked “and I have a boner”_

_“Yeah, and whose fault is that?” But he knew he was fighting against windmills here. Sam was just much more stubborn as him, much more determined and yeah, the sneaky ass’d made sure that Dean wasn’t firing on all cylinders anymore, after that day of orgasms._

_“Please?”_

_“I swear, if you…”_

_Sam nodded, a bit like those stupid dachshounds in the back of some grandma’s car, all eager and happy and Dean couldn’t help but smile a bit. He loved when Sam was happy._

_So he settled back, ignored the twinge of unease when Sam placed the condom and lube next to him and tried to relax._

_And no, it wasn’t easy, because no matter how much Sam babbled supposedly sexy stuff, a finger in his ass felt anything but nice, and even when he hit his prostate – which, dude, cool! – it didn’t make it feel any less weird._

_Oh, he’d had a finger up his ass more than once. There’d been some kinky girls in his life, and some occasions he didn’t think about, but it was still… well, a finger – nope, t w o fingers up his ass._

_“Sam, I think…” but Sam moaned all hot and sexy, and he actually got his tongue down there and yeah, it felt a bit better._

_Ah, well. Might as well enjoy it, right?_

_OoOoOoOo_

_“Ready” Sam was panting, sweating and glistening and a sight to behold. Dean just grunted, turned on his belly and tried not to feel undignified with his ass raised on two pillows, legs spread and Sam’s three very uncomfortable fingers in his asshole. Waiting to be fucked._

_“Condom!” he demanded, and he practically heard the eye-roll. It wasn’t just that Sam was the only one who ever got the clap, but he couldn’t imagine how squishy everything would be once Sam unloaded. It would be a bitch to get clean again. Bad enough there was all that lube in him. It felt fucking weird, to be moist in his ass._

_The wrapper fell to the floor next to Dean’s head and he looked at it, imagined Sam rolling the latex over his huge red cock. He shuddered a bit and started counting dustbunnies in the corner of the room._

_“Ok….” Sam’s voice was husky, and his fingers and lips played over the muscles of Dean’s back, stroking, massaging and kissing. It felt good. Peaceful. Calming. Made him sleepy and warm and –_

_“Holy fu… ow, SAM”_

_“Dean…”_

_“Stopstopstop” he tried to scramble away, clawed at the mattress to get him out under that bulky Sasquatch on top. “Sam…”_

_“Just… Dean, calm down. Calm down, come on, don’t be a pussy!”_

_‘Wait, wasn’t that the whole point, asshole?’ Dean thought, but he was too busy breathing through his nose and calming down again to say it._

_“It’ll get better, just… stay calm, ok? If…if you really can’t take it, if it’s really too much, I’ll stop. But… c’m on…you’ve had worse, right?”_

_‘Yes, Sam, in Hell for example.’ But he’d never stoop so low as to bring it up, and even though he knew it was a cheap trick Sam pulled, he heard and accepted the challenge. He’d get through this, and he’d enjoy it. And he’d not whine about it like a… a… a whiny princess._

_“Cool?”_

_“Yeah, go ‘n”_

_It felt… well. Huge. Like taking a dump backwards, only a lot more painful. He gritted his teeth and clamped his nails into his arms and tried like hell to relax, to let Sam’s fucking dick get into him,_  
  
It hurt. Not Hell-material, far off, but still, it wasn’t good, or sparkly or nice. Didn’t feel sexy or hot. It just felt weird, even as he had relaxed so far that Sam was gliding inside with much less pain involved. Dean felt his insides widen, felt the foreign thing in him, huge and hard and unrelenting. He fought the urge to escape or fight, waited for it to get better, or at least to stop. 

_But Sam was still pushing in, and there couldn’t be more space in there, could there?_

_“Oh…f…ffuck…” Sam moaned above him, and suddenly there was one last, harder push and the whole freaking dick was seated inside, Sam's balls touching his, which felt kinda nice. Would feel better if it wasn’t for that fucking pole in his ass!_

_“Ah, baby… so good.” It was probably considerate to wait a bit, but Dean just wanted to get it over with._

_“Move, Sam. Not gonna break!” and he shifted his hips a bit, gasping at the lightning-quick pleasure-spike that drove through him, gone again before he even appreciated it. It left a deep, hot ache in its wake._

_And then Sam moved._

_He pretty much tuned out the crap Sam said from above, while he pulled his dick out and pushed it in and out and in and yes, sometimes it felt ok, and sometimes it felt a bit like pleasure, but mostly, it felt weird and wrong and … achy. Sure, it wasn’t really that much pain, not after the first entering. But it was not what Dean would label ‘good’, not by any means._

_OoOoOoOoOo_

_“Oh, oh, oh… ah ah ah…” The thrusts grew erratic, the shoves got harder. It felt like a lifetime of getting fucked up the ass, and Dean felt the burn in his legs from being spread so long, the rough bedsheets against his already sensitive skin and the pillows hurting his flaccid dick. He’d been shoved nearly against the wall at the head of the bed, only managed to avoid a concussion because he braced his arms against it. Sam was pushing harder and deeper with every thrust that he made, and Dean was pretty damn sure that he wasn’t gonna sit comfortable for the next few days._

_“Aaahh….”_

_“Oof…” Make that weeks._

_He could feel Sam come inside him, inside the condom which filled and he might’ve imagined it, but it sure felt like it got warmer._

_He groaned when Sam collapsed on him, his dick still inside and Dean just… needed to get away._

_“Sam, move.”_

_Snore._

_“Sam, if you don’t move, I’m gonna move ya, and I don’t care if I rip your fucking dick off in the process!” He brought his elbow up, same time as his head and the combined pain on the forehead and against the ribs woke Sam from his bliss-induced stupor._

_“huh…”_

_“Get off!”_

_Without really caring about Sam’s feelings or cleanliness, Dean wobbled on unsteady legs – mostly from spreading them so long, but also from the pain in his ass – into the bathroom, shut the door and got into the shower._

_OoOoOoOo_

_When he came back out, clean, if still sore and pissed for having been talked into that, Sam sat on the bed, in jogging-pants, cross-legged and looking more delicious than ever before._

_Maybe it was the concern in his eyes. Or the fresh-fucked glow of his skin and the disarrayed hair._

_“Dean…”_

_“Dude, in a long, long line of unsatisfying sex, that one took the cake.” Dean looked up “Sorry,” he added when he saw the misery in Sam’s face._

_“I believe you.”_

_“Yeah?” Dean crossed over to the bed, slowly and carefully sank down and lay back, easing his backside and his muscles. “So next time, it’s your turn?”_

_Sam only nodded, so miserable and unhappy that Dean couldn’t help himself. He pulled him down on top of his chest, patted his back and just slid into slumber, the heartbeat of him his lullaby._

_“Hey, did you call me ‘baby’? Don’t ever call me ‘baby’ again, freak” he mumbled and he felt Sam smile against his skin and finally dropped into dreams._

_**************  
_

Yeah. So that hadn’t been a success. Disappointingly, so had been the reversed sexing, Sam the bottom.

He’d complained the whole time through prepping, the lube was too cold, the fingers too dry, the fingernails too fucking long. Dean had threatened to gag him, which finally shut Sam up.

_  
Okay, turned out sticking your fingers up your lover’s ass, even if it was nice and clean from the shower, felt just as weird as it did having them in his own. Dean’d suppressed his giggles and concentrated on his task, which was… weird. Sure, he’d rubbed Sam’s back and massaged him, he’d given him blowjob after blowjob the whole day so his face ached from the stretch and his throat was hurting from allowing Sam to grab his head and fuck his mouth, but it still didn’t feel anything but weird to thrust your fingers into another man’s backside._

_“Ughs, Dean…” Sam bucked back onto his fingers and Dean raised his eyebrows. Ah, that was that funny spot? He rubbed it some more._

_Sam moaned and groaned, but after two repetitions, Dean, being tuned into Sam’s moods like nobody ever was, knew it was fake. He stopped it and slicked up the … there wasn’t a nicer word for ‘asshole’, was there? Something a bit more sexy?_

_Anyway, he slicked that up and unwrapped the condom. His dick was hard, but it sure had been harder during the day. Seemed his friend had lost a bit of interest here. He jacked it a bit, slowly, imagining Sam’s huge warm hands on it and rolled the latex on. Slicked that as well._

_“Sam, you ok there?” It felt right to ask, and Dean was half hoping Sam would refuse to go through with it._

_“Sure, c’mon, fuck me already” Well, put that way…_

_“Right…”_

_He’d pushed in, and fffffuck, that was tight. And slippery and tight and warm and fucking t i g h t! Dean groaned and Sam moaned, and he tried to stop when he felt Sam tense a bit, clench._

_“Dean… I…”_

_“So who’s calling who a pussy now?” No way would Dean get fucked without Sam getting some as well. No way!_

_“Jerk!”_

_“Prin-“ and Dean pushed in the whole way “-cess!”_

_Sensation ripped through him, mostly ‘hot’, ‘tight’ and ‘igh, I got my dick in Sam’s ass’. The hot and tight was a nice feel, but the ass-part… Dean decided then and there that he really, really liked pussy better. There seemed to be no substitute._

_“Ow, damn, move!”_

_“Stop whining, bitch” he smirked back, his breath hitching when Sam just clamped his muscles in response._

_OoOoOoOoOo_

_It was hard work, to get off inside Sam’s ass. It never took so long to get that prickly feeling in his spine when Sam was sucking him, or jacking him off. Hell, he’d come sooner that day Sam had decided to make him come from licking and kissing and never touching his dick!_

_So he pushed and thrust and retreated and got back in, the sensation not bad but still unsatisfying._

_And he freaking knew Sam wasn’t enjoying himself down there, he didn’t need to look. In fact, he refused to look because anything that reminded him of the fact that he was sticking his cock in someone’s asshole turned him off so quickly that he wouldn’t be able to come any time soon._

_In the end, it took imagining the slippery wetness and sweet smell of some girl’s pussy to come, and even that was a bit disappointing after all the work he’d had to do._

_Sam groaned, not in happy bliss, that was for sure, and stood, shuffling awkwardly to the bathroom. Dean cleaned himself off, got rid of the condom and put his boxers back on. He sat on the bed, much like Sam had done the day their roles had been reversed._

_The lock clicked open, and the big, stunning man who emerged made Dean’s mouth water. No, it wasn’t Sam that was the problem, or the fact that he was bedding a guy. He enjoyed anything else they did, the touches and the kisses and hell, even the cuddling. But buttfucking seemed not to be his kink._

_Sam looked at him, and like in earlier times he ducked his head, shying away a bit from Dean’s gaze._

_“I gather you didn’t like that much, huh?”_

_Sam only gave a pained grin._

__

****************

They’d tried it again, different surrounding, better beds. Different mood. They switched places, determined to finally enjoy the fucking, no matter what. They made it a challenge, changed positions, tried it in the day and in the night and in the afternoon, but it didn’t matter.

On their seventh try, Sam on the bottom, Dean just gave up mid-thrust.

Just stopped going, pulled out – still a bit hard – and rolled on his back, arm over his eyes.

“Hey, what?”

“This is stupid, Sam.”

“What, I was just getting into it…”

“Stop right there!” Dean growled, raised himself on his elbows and furiously took in his face. “You’re not enjoying yourself, you hate it. I hate it when you fuck me, and I know you do too, so the only thing we’re getting a hang on here is perfecting our fake orgasm!”

“Where’s that suddenly coming from. You think I’m faking…”

“Fuck, Sam, the only way I can get off when I stick my dick inside your ass is to close my eyes and imagine a fucking _cunt_ that I’m fucking!”

It was cruel to say that, and he knew it from the flinch Sam made when he’d flung that into his face. Dean stood and paced around the room, hands through his hair, furiously thinking how to make that alright, how to take it back, apologize. Because Sam wasn’t a bad lay, he wasn’t! He featured in any wet dream Dean had these days, his face, his body and his voice whispering sweet, dirty things in his ear while nibbling his earlobe. Sam was who he dreamed of, who he wanted to be with for the rest of their lives, with all that was Sam, his bitching and whining and complaining, his loving, his caring and his wicked-smart planning. His sharp mind and sharp tongue, his sweet words and his gentle hands.

He didn’t want to lose that, and hell, he’d let himself get fucked up his ass forever if that was what it took to keep him. After all, he’d already let himself get fucked by demons for that guy, so this was nothing.

“Sam…”

“Jessica.” What?

“What?”

“It’s Jess I imagine.”

Wow. That was a sucker-punch. Dean felt it in his guts, his spine seemed to contract in sharp pain when he heard that, because even when he himself had just said something similar, it hurt. Maybe he should feel grateful that it wasn’t Ruby, but… yeah. Ouch.

“Dean, look at me, c’mon”

He did, because he owed him that much. And he was glad when he did, because there wasn’t pity in Sam’s gaze, only love and understanding.

“Dean, it’s not Jess I see when I watch you. When I feel like the world is bursting because life is so good, it’s not her I see. It’s not Jessica I wanna spend my life with, hasn’t been for a long time. And it’s not Jessica that makes me feel warm inside when I hold her, or when I listen to her snore. I loved her, once upon a time, but that’s not now. And I swear to you, as much as I’m sure you would, that I certainly don’t imagine her in my dreams, awake or not. When I see you move, I wanna touch you, wanna run my hands down your side and I wanna make you shiver like you do, wanna make you close your eyes and moan and I wanna make you lose yourself and give you whatever it takes to make you feel like you deserve to feel, whatever it fucking takes.  
So, if it’d take you fucking me, or if it’d take me fucking you, I’d do that. I’d fuck you if that’s what you want, and I’d let you fuck me if that’s what it takes to keep you. But honestly, it’s not what I personally like that much. Neither of those is.”

Dean stood against the table, Sam just in front of him, all emotion, all love and a hint of concern. And he couldn’t help himself.

He chuckled.

“Man, we’re really screwed-up, aren’t we? C’mere, Sam.” He wrapped him in his arms, held him tight and let his face sink into that place underneath Sam’s jaw, in that dip between collarbone and neck. _His_ place, because it was just made for him, he fit right in. Dean smelled the sweet scent of his love, a bit sweaty right now and suddenly he was aware of his now-flaccid dick, still wrapped in a lubed condom, and he laughed.

“This is ridiculous. Who says we need to stick our dicks inside our asses anyway, huh?” Sam murmured. “We were just happy before, why change that when we both don’t like it?”

“You started it!”

“Yeah, and we both are ending it. If you agree…”

Dean nodded and sighed.

“Now, I think we’ve got something to finish, haven’t we?” Sam smirked into his ear, and even before Dean could process, he felt that wonderful, wonderful Samsquatch-paw on his dick, pulling off the condom and slowly, oh-so-slowly jacking him. Dean leaned back against the table, his hands holding him in place because he’d melt and sink to the floor if they didn’t, and before he even knew it, Sam did just that, dropped to his naked knees on the dirty vinyl-carpet and wrapped his lips over Dean's cock, warm and slippery and perfect.

He looked down, into Sam’s face, his eyes meeting Dean’s with compassion and so much freaking love that Dean came, hard and long and with so much force that his knees buckled and his hands lost their strength to hold him up.

When he was back from lala-land, Sam was holding him. They were both on the floor, both on their knees, Dean pliant and loose and warm and so freaking happy, wrapped up in Sam’s grip, his head on his love’s shoulder, his arms loosely around Sam’s back.

“Love you, love you, love you, never anyone else, this is perfect, this is what I want, this is what I need” Sam was whispering in his ear, and Dean smiled and tightened his grip. From Sam’s abrupt hitch in his breath, he knew those words hadn’t been meant to be heard, but Dean was glad that he did.

"Me too" he whispered and smoothed his hands over Sam's sweat-sticky back. "Me too"

End.


End file.
